Verified against ChatGPT · 2026-08-07
Run an honest post-mortem on a lost deal before writing it off as "budget"
Turn your deal history and notes on a lost deal into a real post-mortem tested against actual loss-reason categories, instead of accepting the reflexive one-word reason logged and forgotten.
The prompt
Ready to copy — highlighted parts are example details you can swap.
We lost this deal: Greymoor Industrial, logged reason "lost to competitor". Deal history/notes: strong first two calls, champion went quiet after their VP reorg was announced, one follow-up email got a one-line reply, then nothing; we assumed they picked a competitor. Stage at time of loss: proposal sent, awaiting signature. Run a real post-mortem, not a rubber-stamp of the logged reason: 1. Test the logged reason "lost to competitor" against strong first two calls, champion went quiet after their VP reorg was announced, one follow-up email got a one-line reply, then nothing; we assumed they picked a competitor — does the evidence actually support it, or does it look like a proxy for something else (the most common example: a deal logged as "lost to competitor" or "budget" that was actually "no decision" — the prospect did nothing rather than actively choosing an alternative)? 2. Identify the earliest point in strong first two calls, champion went quiet after their VP reorg was announced, one follow-up email got a one-line reply, then nothing; we assumed they picked a competitor where this deal was already at risk, even if it didn't look like it then — a specific stage or interaction, not "communication could have been better." 3. Name ONE thing that, if done differently at that point, plausibly changes the outcome — must be specific and actionable, not "should have built more urgency." 4. Name ONE thing that was actually outside our control, so the takeaway isn't "everything was our fault." Then give me a one-line lesson I could apply to the next deal at a similar stage — the kind of thing worth saying out loud in a pipeline review, not a vague "stay closer to the champion."
Customize the highlighted detailsoptional — the prompt above already works
Why this works
Testing the logged reason against the actual evidence targets a well-documented pattern in B2B win/loss analysis: "no decision" — the prospect simply going quiet rather than actively choosing a competitor — is consistently one of the most common real outcomes in competitive deals, far more often than reps log it, because "lost to Competitor X" is a less uncomfortable box to check than "I never got a next step after their reorg." Forcing the model to name one in-control and one out-of-control factor prevents both failure modes of a post-mortem: the self-flagellating version that blames the rep for everything, and the defensive version that blames the market for everything — neither produces a lesson anyone can actually apply to the next deal.
What you get back
The evidence doesn't clearly support "lost to competitor" — there's no mention of a competitor anywhere in the deal history, only a VP reorg followed by silence. This looks more like "no decision," with the reorg as the likely cause. Earliest risk point: the champion going quiet after the reorg was announced, with no attempt to identify a new stakeholder. Lesson: when a champion's org changes mid-deal, treat it as a re-qualification trigger, not a delay to wait out.
Verified against
ChatGPT GPT-5.1 · 2026-08-07
Claude Sonnet 4.5 · 2026-08-07
Changelog
- 2026-08-07 — Initial version, verified against GPT-5.1 and Claude Sonnet 4.5.
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